2-(2-Hydroxyethyl)indoline → (RS)-2-(2-Hydroxyethyl)-N-(3-methylisoquinol-5-yl)indoline-1-carbothioamide

HRID 443806Notes

Reaction equation

HRID 443806 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5]1.[N:13]([C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[CH:18]=[C:19]([CH3:26])[N:20]=[CH:21]2)=[C:14]=[S:15]>C(O)C>[OH:1][CH2:2][CH2:3][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]1[C:14](=[S:15])[NH:13][C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[CH:18]=[C:19]([CH3:26])[N:20]=[CH:21]2

Participants

4

Reactant 2

HCID 130143192-(2-Hydroxyethyl)indolineHCID 130143215-Isothiocyanato-3-methylisoquinoline

Product 1

HCID 13014324(RS)-2-(2-Hydroxyethyl)-N-(3-methylisoquinol-5-yl)indoline-1-carbothioamideYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(2-Hydroxyethyl)indoline (43 g) and 5-isothiocyanato-3-methylisoquinoline (52 g) are dissolved in ethanol (800 cc). The solution, which is kept for 24 hours at a temperature of about 20° C., deposits a solid which is isolated by filtration, washed with ethanol (3×50 cc) and dried. (RS)-2-(2-Hydroxyethyl)-N-(3-methylisoquinol-5-yl)indoline-1-carbothioamide (51 g), a white solid, is obtained.

Workup

  1. customis isolated by filtration
  2. washwashed with ethanol (3×50 cc)
  3. customdried

Sources & evidence

ORD record
ord-7f0b1f16aab8485aa9786e837a80ea9c
Source dataset
uspto-grants-1981_04
Patent number
US04261993

Reaction notes

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